Catalytic asymmetric oxa-Diels-Alder reaction of acroleins with simple alkenes.

ABSTRACT: The catalytic asymmetric inverse-electron-demand oxa-Diels-Alder (IODA) reaction is a highly effective synthetic method for creating enantioenriched six-membered oxygen-containing heterocycles. Despite significant effort in this area, simple α,β-unsaturated aldehydes/ketones and nonpolarized alkenes are seldom utilized as substrates due to their low reactivity and difficulties in achieving enantiocontrol. This report describes an intermolecular asymmetric IODA reaction between α-bromoacroleins and neutral alkenes that is catalyzed by oxazaborolidinium cation 1f. The resulting dihydropyrans are produced in high yields and excellent enantioselectivities over a broad range of substrates. The use of acrolein in the IODA reaction produces 3,4-dihydropyran with an unoccupied C6 position in the r

SUBMITTER: Zeng L 

PROVIDER: S-EPMC10267187 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature